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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24O
Molecular Weight 220.3505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLATED HYDROXYTOLUENE

SMILES

CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

InChI

InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

HIDE SMILES / InChI

Molecular Formula C15H24O
Molecular Weight 220.3505
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.

CNS Activity

Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms

Approval Year

PubMed

PubMed

TitleDatePubMed
Haemorrhages due to defective blood coagulation do not occur in mice and guinea-pigs fed butylated hydroxytoluene, but nephrotoxicity is found in mice.
1992 Feb
Practical synthesis of chiral emopamil left hand as a bioactive motif.
2002 Aug 23
Ammonia-induced heme oxygenase-1 expression in cultured rat astrocytes and rat brain in vivo.
2002 Dec
[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography].
2002 Jul
Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations.
2002 Jul 11
Molecular profiling of genes up-regulated during promotion by phenobarbital treatment in a medium-term rat liver bioassay.
2002 Jun
Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS.
2002 May
A convenient method for determination of the C20-22 PUFA composition of glycerolipids in blood and breast milk.
2002 May
Celecoxib reduces pulmonary inflammation but not lung tumorigenesis in mice.
2002 Oct
Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey.
2003 Dec
Antioxidizing potency of phenol compounds in olive oil mill wastewater.
2003 Dec 17
Free radical-induced protein modification and inhibition of Ca2+-ATPase of cardiac sarcoplasmic reticulum.
2003 Jun
Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys.
2003 May
Trapping effect of synthetic sex pheromone of Acleris fimbriana (Lepidoptera: Tortricidae) in Chinese northern orchard.
2003 May-Jun
Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).
2003 Nov-Dec
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
2004 Apr
Recovery of phenolic antioxidants from wine industry by-products.
2004 Apr
Structure and generation mechanism of a novel degradation product formed by oxidatively induced coupling of miconazole nitrate with butylated hydroxytoluene in a topical ointment studied by HPLC-ESI-MS and organic synthesis.
2004 Feb
A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants.
2004 Feb 20
Analysis of insecticidal Azadirachta indica A. Juss. fractions.
2004 Jan-Feb
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.
2004 Jul
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.
2004 Jun
Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes.
2004 Jun
Inhibitory effects of organic acid salts on growth of Clostridium perfringens from spore inocula during chilling of marinated ground turkey breast.
2004 Jun 1
In vitro estrogenicity of resin composites.
2004 Mar
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Relative antioxidant capacities of propofol and its main metabolites.
2004 Nov
Optimization of a high-performance liquid chromatography system by artificial neural networks for separation and determination of antioxidants.
2004 Oct
Mononuclear, five-coordinate lanthanide amido and aryloxide complexes bearing tetradentate (N2O2) Schiff bases.
2004 Oct 4
Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation.
2004 Sep 22
Anticancer properties of propofol-docosahexaenoate and propofol-eicosapentaenoate on breast cancer cells.
2005
2,1,3-Benzothiadiazine derivatives: synthesis and screening versus PDE4 enzyme.
2005 Aug
Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors.
2005 Feb 15
Synthesis and characterization of BHT-derived tert-butyl dendrons.
2005 Feb 4
TNF alpha potentiates glutamate neurotoxicity by inhibiting glutamate uptake in organotypic brain slice cultures: neuroprotection by NF kappa B inhibition.
2005 Feb 9
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.
2005 Jan 26
Single-site anionic polymerization. Monomeric ester enolaluminate propagator synthesis, molecular structure, and polymerization mechanism.
2005 Jan 26
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.
2005 Oct
Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats.
2005 Oct 1
New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.
2006 Aug 15
Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures.
2006 Jan 6
Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species.
2006 Jul 1
Attenuation of the pulmonary inflammatory response following butylated hydroxytoluene treatment of cytosolic phospholipase A2 null mice.
2006 Jun
Synthesis and antioxidant activity of [60]fullerene-BHT conjugates.
2006 Jun 2
Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages.
2006 Jun 26
Cadmium-induced apoptosis in rat kidney epithelial cells involves decrease in nuclear factor-kappa B activity.
2006 May
Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside.
2006 May 31
Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems.
2006 May 31
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways?
2007 May-Jun
Patents

Sample Use Guides

The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:02 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:02 GMT 2023
Record UNII
1P9D0Z171K
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLATED HYDROXYTOLUENE
FHFI   HSDB   II   MART.   MI   NF   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
Butylated hydroxytoluene [WHO-DD]
Common Name English
BUTYLATED HYDROXYTOLUENE [USP-RS]
Common Name English
INS NO.321
Code English
BUTYLATED HYDROXYTOLUENE [II]
Common Name English
BUTYLHYDROXYTOLUENE [EP MONOGRAPH]
Common Name English
E-321
Code English
PHENOL, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-
Systematic Name English
BUTYLATED HYDROXYTOLUENE [VANDF]
Common Name English
BUTYLATED HYDROXYTOLUENE (E 321)
Common Name English
BUTYLATED HYDROXYTOLUENE [FHFI]
Common Name English
BUTYLHYDROXYTOLUENE
EP  
Systematic Name English
2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYLPHENOL
Systematic Name English
BUTYLATED HYDROXYTOLUENE [IARC]
Common Name English
BUTYLATED HYDROXYTOLUENE [MART.]
Common Name English
BHT [FCC]
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL
Common Name English
KERABIT
Common Name English
BUTYLATED HYDROXYTOLUENE [NF]
Common Name English
4-METHYL-2,6-DITERTIARY-BUTYL-PHENOL
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-PHENOL
Systematic Name English
NSC-6347
Code English
BUTYLATED HYDROXYTOLUENE [HSDB]
Common Name English
FEMA NO. 2184
Code English
BHT
FCC   INCI  
INCI  
Official Name English
BUTYLATED HYDROXYTOLUENE [MI]
Common Name English
INS-321
Code English
2,6-DITERTIARY-BUTYL-P-CRESOL
Common Name English
BUTYLATED HYDROXYTOLUENE [WHO-IP]
Common Name English
BHT [INCI]
Common Name English
BUTYLHYDROXYTOLUENUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 22105
Created by admin on Fri Dec 15 15:08:02 GMT 2023 , Edited by admin on Fri Dec 15 15:08:02 GMT 2023
JECFA EVALUATION INS-321
Created by admin on Fri Dec 15 15:08:02 GMT 2023 , Edited by admin on Fri Dec 15 15:08:02 GMT 2023
CODEX ALIMENTARIUS (GSFA) INS-321
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NCI_THESAURUS C275
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CFR 21 CFR 172.115
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Code System Code Type Description
CHEBI
34247
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PRIMARY
MERCK INDEX
m2820
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PRIMARY Merck Index
SMS_ID
100000076384
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PRIMARY
ChEMBL
CHEMBL146
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PRIMARY
NSC
6347
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PRIMARY
MESH
D002084
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PRIMARY
EVMPD
SUB11765MIG
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PRIMARY
RS_ITEM_NUM
1082708
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PRIMARY
NCI_THESAURUS
C322
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PRIMARY
DAILYMED
1P9D0Z171K
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PRIMARY
FDA UNII
1P9D0Z171K
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PRIMARY
CAS
128-37-0
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PRIMARY
ECHA (EC/EINECS)
204-881-4
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PRIMARY
EPA CompTox
DTXSID2020216
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PRIMARY
WIKIPEDIA
BUTYLATED HYDROXYTOLUENE
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY
RXCUI
1848
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY RxNorm
HSDB
1147
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PRIMARY
PUBCHEM
31404
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BUTYLATED HYDROXYTOLUENE
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light.
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METABOLITE -> PARENT
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Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.65.pdf